Advice needed re: Stratton (ME 27) to Rangley (ME 4) section

I am likely going to split this into three SOBO hikes using the Sugarloaf lift for Hike 1.

Hike 1: Overnight hike -- Sugarloaf to ME4, 22.5 miles (22 AT + .5 other).

Will probably start mid-day Saturday, and need to stealth camp near Orbeton Stream/Railroad Bed after a mostly downhill 9 mile day. Suggestions on terrain, water, campsites would be appreciated. Then 13 miles on Sunday, pretty much up and down Saddleback peaks (Saddleback Jr., Horn, Saddleback Mtn.), would like to finish by 6 PM if possible. Sanity check on distance needed (for perspective, was doing 20 milers pretty comfortably in Vermont in June, but a 14+ miler in Northern Presidentials--Joe Dodge Lodge to Lake in the Clouds hut, missing Mt. Washington summit--pretty much kicked my butt, and up/down Katadhin took me about 11 hours on Sunday, a perfect day).

Hike 2: Day hike Caribou Valley Road to Sugarloaf Base, descending via trail to base, 6-7 miles (2.5 steeply uphill AT miles, plus miles to get to base).

Hike 3: Day hike ME 27 (or from road crossing 1 mile to the north) to Caribou Valley Road (8-9 AT miles).

As for hikes 2-3, any advice on terrain and current condition of Caribou Valley Road (and parking) would be appreciated. I have updates from about a month ago on the road (i.e., was passable), but an update would be nice.

Thanks!

I didn't find that section as difficult as advertised. I stayed at the Maine Roadhouse and had Sue shuttle me to ME 4. Original plan was Spaulding Mtn lean-to (18.5m) but I made such great time I ended up staying in the warming hut (may not be there anymore) on top of Sugarloaf (22+ miles). Next day I rolled down to ME 27 and got picked up around noon I think.

It's not as tough as the stretch heading up to or down Mt Washington.

Good, I might push to the shelter then, and might combine hikes 2 & 3. I plan to work in the PMs, so that is why I have the short hikes planned.